Question

1) (20 points) A certain graduate student needs to make 2-chloropropane. Worried about the selectivity problems that occur wh

Potentially Useful Information R= 8.314 J/mol K BDEs (in kJ/mol) C-H BDES C-C BDES Other BDES 436 293 410 CH3-CH3 CH2=CH HC=C

a) Show the mechanism for the free radical chlorination of bromopropane. Clearly show the initiation, propagation, and termination steps.

b) Use the BDEs shown on page 1 to calculate the enthalpy change for this reaction.

c) Unfortunately, the student’s attempt in question 3 failed, and he only made traces of 2- chloropropane by using this approach. What was the major product of the reaction, and explain why it was formed instead. You may find the BDEs on page 1 to be helpful again.

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Answer #1

ay Br t BY- Cu Dni tiolion ii t ci Bropagatgins Br + Br-ce ce Termination + Bry + C2 Br-a T-2 1-335-(-243)-(-285) -26 KJ/mol Ove energy becaune nern BDE is Yeleare whe Thw n&is fpemed 4H- Ove Haj on Product Tuitiatio

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